Down at Our Rendezvous
by fagur fiskur
Summary: In which Dean gets picked up by Anna and Ruby for a fun night and Dean and Cas have the world's most awkward meet cute the morning after. Dean/Castiel, Anna/Ruby, Anna/Ruby/Dean.
1. Come and Knock on Our Door

**A/N:** Basically this is just a porny set-up for Dean and Cas to have the world's most awkward meet cute. Although I do love the hell out of Anna/Ruby, don't get me wrong.

Title is taken from the Three's Company theme song (feeling super tacky right now but whatevs).

Many thanks to jademac2442 for beta reading!

* * *

**Part 1: Come and Knock on Our Door**

* * *

So it had taken Ruby a while to get down with the whole monogamy thing. Prior to Anna, the longest relationship of her life had been with a bottle of whiskey, and that had only lasted so long because it was the bottom-shelf, near undrinkable crap that Meg had gotten her as a housewarming gift.

But Ruby liked Anna. Really liked her. Maybe even more than liked, but that was not something Ruby was ready to think about yet, let alone talk about.

What with her really liking Anna (and possibly more than just liking), Ruby had decided to make an effort. In the end, it turned out that monogamy wasn't such an effort. When you really liked someone, you didn't want to have sex with anyone else. Who'd have guessed?

But then Anna dropped the bomb.

"I want to have a threesome."

Ruby nearly choked on her bacon strip. She coughed a couple of times and managed to keep it down, thank God. This bacon was good bacon. Anna's big brother happened to be excellent at breakfast foods even if he sucked in most other ways (including in the bedroom, hey-o). "What?"

Anna shrugged. "A threesome. I want to have one."

"Why?" Ruby asked. What was Anna getting at? Was she not enough anymore, was that what she was saying? Oh God, was she going to get dumped while her girlfriend had sex with some chick or dude they picked up at the bar?

"I just think it'd be fun." Anna smiled. "I kind of can't get the image of you riding some guy's face while I ride his cock out of my head."

Oh. Okay. This, Ruby could get with. She could sort of see where Anna was coming from. Ruby plus some random dude didn't really do it for her, true, but Ruby plus her girlfriend plus some random dude? That had potential. Especially accompanied with Anna's coy smile and dirty words.

"Okay, I'm in." Ruby pushed aside her plate. "You know, I can think of something I'd much rather be eating than this."

* * *

Ruby had figured her days of trawling the club for one-night-stands were over. She had made her peace with that. Being back out on the scene was a little weird, but being there with Anna helped. They split up as soon as they got inside, Anna's idea so as not to come off as too predatory, keeping each other in sight all the same. Anna headed for the dance floor, while Ruby headed for the bar.

Not half a minute later, she spotted him.

He was alone by the bar, nursing a glass of whiskey, not-so-subtly checking out a group of women dancing in a group nearby . He looked like an Abercrombie and Fich model, but his clothes screamed Goodwill and he had a big-ass scar across his left forearm. His forearm, which Ruby noted, was bulging with notable muscle. She licked her lips. How a treat like that hadn't been picked already, she didn't get, but hey. Their loss, her and Anna's gain.

"Hello there, handsome," she drawled, sliding up on the stool next to him.

The stranger shot her an assessing glance. His eyes were pretty and green; not quite to Ruby's taste (big and brown) but nice all the same. "Aren't you a sight for sore eyes."

Ruby rolled her eyes. If he wasn't so hot, she would have passed the guy over for a line that cheap. "I'm Ruby."

"Dean," the stranger, Dean, said. He smiled, charming and easy. "You come over here so I could buy you a drink?"

"Actually, I was thinking I could invite you over for a drink instead," Ruby said casually. "Me and my girlfriend were gonna make a night of it, but we wouldn't say no to some company."

Ruby could pinpoint the exact moment Dean got it, just what he was being offered. He swallowed, looking kind of nervous. "That so."

"Mhm." Ruby glanced back at the dance floor, catching Anna's eyes and gesturing for her to come over. "What do you say?"

Dean looked over his shoulder to see what Ruby was looking at, and his eyes widened slightly. What had he expected, that Ruby was shacking up with some troll?

"Hey babe," Ruby greeted, smiling lasciviously. Anna rolled her eyes but she was clearly feeling indulgent, so she smiled back. Then her eyes fell on Dean and, yeah, she liked what she saw. "Anna, this is my new friend, Dean. Dean, this is Anna."

To Dean's credit, he recovered remarkably. He eyed Anna in a way that Ruby would have normally smacked him for, but circumstances were different and it was obvious that Anna returned his interest. "Pleasure to meet you."

"The pleasure is all mine," Anna replied, sitting down at the bar without taking her eyes off of Dean. Ruby would have felt pretty excluded, if Anna's hand hadn't landed on her thigh, squeezing it softly. On the surface, Dean may have held her attention well enough, but Anna's body would always seek out Ruby's first and foremost.

"So," Ruby purred. "Come grab a drink with us at our place? I promise we won't take advantage of you in your drunken state. Well," the left corner of her mouth quirked in a predatory smirk, "not unless you want us to."

Dean's eyes darted between the two of them. For a second, Ruby was almost sure that he was going to tell them thanks but no thanks, but then that confident, easy grin was back. "Hell, I can't refuse two such lovely ladies anything. Sure, why not."

Ruby felt Anna's hand squeezing her thigh again. This was going to be a good night.

* * *

Ruby had worried a bit about how this would all happen. Would they sit around the apartment, awkwardly sipping at their drinks while they tried to figure out the logistics of this? But as it turned out, she need not have worried, because as soon as the doors were closed, Anna was pushing her against them and kissing the living daylights out of her.

Ruby kissed back because, hey, Anna's tongue was in her mouth and that was never not awesome. Then she remembered her manners and broke the kiss. Anna's lips went for her jawline instead, and Ruby looked over at Dean, who was standing there looking like he didn't quite know what to do with himself.

Ruby could help with that.

"Come here," she commanded.

Dean stepped over, cautious and slow, and as soon as he was in reach, Ruby grabbed his hand and pulled him close so that Anna was squeezed between them. Judging by the soft sound she made against Ruby's throat, she did not mind one bit. Ruby tugged at Dean's hand and put it around Anna's waist, then grabbed the back of his head and pulled him in for a kiss.

It was different than kissing Anna, obviously. His lips were chapped and he had stubble but hey, Ruby'd never been one to complain about a beard burn. He was a good kisser, not as good as Anna, but he had technique. He didn't slobber all over Ruby, thinking the more tongue the better, as most guys seemed to. He was teasing and soft, and at Ruby's silent insistence, let her take over the kiss.

They came up for air. Ruby could feel Anna's hips move against hers, which was good, but then she looked down and saw that she was grinding her ass against Dean's erection, which was even better.

"Let's move this to the bedroom," Anna suggested in a breathy voice and Ruby had to grind a couple of seconds more before she was ready to let her go.

"Let's," she agreed. Dean made some noise that she assumed meant he was up for it.

Anna grabbed Dean's hand and led him to the bedroom. Ruby trailed behind, kicking off her shoes and pulling off her shirt on the way. She was almost done unhooking her bra when she got inside, slamming the door shut behind her. Anna had ordered her brother to stay out tonight, but you never knew. Ruby figured it was better to be safe than sorry. She'd traumatized the poor bastard enough during the last few months.

"Undress her," Ruby ordered lazily. Dean hesitated, flushing (and Ruby was really looking forward to seeing just how far down that flush went), then started by pushing Anna gently onto the bed, kneeling over her and pulling off her socks. His movements were smooth and sure, but he was biting his bottom lip and still flushing like a school girl and, well. Even Ruby had to admit that she was affected by the sight.

Though not nearly as much as she was by Anna, all spread out on the bed, hair messy and chest heaving, being divested of her clothes one piece at a time. She looked like the stuff wet dreams are made of, and Ruby couldn't wait to see her bouncing on Dean's lap. Anna had a pretty impressive poker face and she was not quick to show emotion, so seeing her fall apart in bed was all the more delicious.

Ruby shucked off her pants and panties. She walked up to the bed and crawls up behind Dean, pressing her breast against his back and hooking her chin over his shoulder. He'd just finished pulling off Anna's panties, leaving her naked and him the only one still clothed.

"Very good," Ruby whispered into his ear.

She bit his earlobe softly, just to feel him shudder, and snuck one hand underneath his t-shirt. Locking eyes with Anna, who was grinning and softly stroking her long, long legs, Ruby searched out one of Dean's nipples and pinched it. His hips stuttered slightly, but he didn't make a sound. That wouldn't do.

"Clothes off," Ruby said. She stood back up and walked towards the nightstand. They had a veritable pile of treasure in that drawer but for now, Ruby contented herself with the lube and condoms. Dean seemed like a pretty vanilla guy, threesome with a hot lesbian couple notwithstanding, and she didn't want to freak him out.

On the bed, Dean was removing his belt. Underneath him, Anna was still teasing herself, fingers trailing patterns on her inner thigh. Her eyes were intent on Dean, enjoying the show, but she looked up when she saw Ruby coming and gave her a not-so-subtle once-over, smiling coyly.

"Listen up, kids, 'cause I'm only gonna explain this to you once," Ruby said.

"Anyone ever tell you you're kind of bossy?" Dean muttered, sliding the zipper on his pants down.

"Oh, you know you love it." Ruby got back on the bed, a happy swing in her hips. "You're going to get Anna hot and ready, 'cause it's been a while since she had anything up there bigger than my fingers and if you're proportional, this isn't going to be easy on her if you just dive straight in."

Dean raised a single eyebrow and wiggled out of his underwear, proving that not only was he proportional, but he also had a fantastic ass.

"Then I want you to lie down so she can ride your cock while I ride your face." Ruby grinned. "Sound good?"

Instead of waiting for an answer, she handed Dean the lube and condom, then climbed over to straddle Anna's waist and kiss her. Anna surged into the kiss, moaning happily. She gasped and Ruby peeked over her shoulder to see that Dean was sucking little marks onto Anna's thighs and stroking her, one finger already inside her. The sight of someone else's fingers in her girlfriend should have probably made Ruby jealous, but it only got her hotter; Dean's fingers so nice and big and Anna all tight and pink around him.

Ruby was too busy watching to notice Anna's wandering hands until she was being penetrated by two of Anna's fingers at once. There was only the slightest pinch; Ruby was already excited from watching Dean and Anna and getting to order them around. And speaking of...

"Lick her pussy, but don't touch her clit yet," Ruby ordered, knowing how Anna liked to be teased.

Anna pouted and pulled Ruby down for another kiss. It was sloppy and eager, but Anna's fingers were still sure and precise inside Ruby. The movements sent warm shocks of pleasure rocketing through her body. In retaliation, Ruby sucked on Anna's tongue and pinched her nipples. She was far from gentle and when Anna moaned against her mouth, she wished she'd at least gotten the nipple clamps out.

Ruby broke the kiss and turned her head.

Dean had three fingers inside Anna now, and he was licking softly at her labia; soft, short little licks that couldn't be bringing any sort of relief. Anna whined and ground upwards, hindered by Ruby's weight on her. Ruby pressed her back against the bed with one hand on her chest. Absentmindedly, she flicked at Anna's nipple, and grinned when Anna tried to buck up again. Nothing better than having her girl beneath her all hot and bothered, completely under her control.

"Dean," Ruby said, "on your back. Anna, sit up."

They both scrambled to get into position and as he crawled past her, Ruby couldn't resist the temptation and gave Dean's ass a nice, hard smack. Judging by the barely bit back moan, he didn't totally hate it, and Ruby filed that information for use later in the evening.

Dean had already rolled the condom onto his cock. Anna gave it a couple of strokes, then moved to straddle him. Ruby couldn't take her eyes off the rapturous expression on her face as her girlfriend lowered herself onto Dean's cock, until she'd taken him all the way in.

"Fuck," Anna sighed.

"Fuck," Dean echoed.

He reached his hands out and wrapped them around Anna's hips, not steering her, just supporting.

Ruby crawled onto the bed, nipping at Anna's neck as she passed her. She raised an eyebrow at Dean, silently asking for an okay, and he grinned cockily back, so she straddled his head, reaching back to grab at the headboard as she lowered herself. She stopped when she felt his breath hit her, the sensation a kind of gentle tease that made her tingle and get just a bit wetter.

Then his tongue was surging up, teasing at her folds and she had to remind herself not to sink all the way down. Instead, she began to gently grind her hips to help him hit all the right spots, feeling him groan. Anna started to move as well. Ruby couldn't resist leaning forward to finger at her clit and Anna moaned loudly, lifting herself off of Dean's lap and slamming back down.

"Come on," Ruby muttered, unsure whether Dean was avoiding her clit on purpose or if he was just that bad at it. She felt him grin against her and then - oh.

He licked over her, tongue pointed and wriggling and it was just this side of too much sensation, before he moved back to tracing her folds. He moved one hand from Anna's hips, who was now bouncing in his lap and it really was amazing he could focus so intently on Ruby, given how she must have felt around him.

He spread her and started to just go at it, licking messily and with no finesse, spreading his tongue to cover as large an area as he could and then pointing it again and teasing her clit as he penetrated her with two fingers, delving deep and crooking to find her g-spot. Ruby moaned when he found it and tugged at Anna until she was leaning forward, too, and they could share a messy, open mouthed kiss.

Ruby was hurtling quickly towards orgasm now - she'd always been sensitive, and nothing felt quite as good too her as a tongue on her clit and two fingers inside her, filling her without being uncomfortably intrusive. "That's it," she moaned in encouragement. "Oh God, right there, just like that, c'mon..."

Then Anna lowered her mouth and sucked on her nipple, and Ruby was just done. She climaxed silently, and it took everything she had not to sit down on Dean's face. She clumsily moved off of him, legs weak and shaking, body still tingling pleasantly. "Good boy," she praised with a grin, making Anna giggle and Dean's hips stutter.

She kissed Anna again. "Get off his lap," she commanded. "I have something else planned for him, and you're gonna wanna feel that mouth on you."

Anna obeyed without question, although Dean whined in protest.

"Relax, big boy," Ruby said. "Get your head between her thighs, m'kay? I need to get something from my treasure chest."

Anna leaned against the headboard, legs spread obscenely. Dean didn't need to be told twice and he was on her in the next second, groaning enthusiastically.

Ruby opened the night stand drawer and pulled out her strap-on. It was purple and slightly curved, about six inches long. Not the biggest toy in Ruby's collection, but plenty intimidating for a straight boy. She strapped on the harness and crawled up behind Dean, letting it poke him in the thigh. He looked up, eyes wide.

"What are you-"

"Shh," Ruby cut him off. "You'll enjoy it, I promise. Besides, I need to prep you first. If you don't like that, I'll stop."

Dean still looked skeptical, so Ruby helpfully pushed his head back between Anna's thighs, giving him something else to focus on. She poured a liberal amount of lube on her fingers, warmed it in her hands. Then she grabbed hold of his hips, pulling his legs apart. He resisted slightly and she kissed his thigh, comforting. "That's a good boy."

She stroked his hole, feeling it twitch underneath her fingertips. She carefully inserted one finger, going slow and steady. His legs fell more open and she grinned. Pumped her finger inside him a few times, feeling him loosen slowly around her, then inserted another, scissoring them.

Dean was moaning now, the sound muffled.

"Knew you'd like it," Ruby said smugly. "Having someone fill you up, stretch you out. Such a good little cockslut."

It was twisted that she got off talking to guys like this, when she'd always hated being called these names. She'd never talked to Anna this way, choosing instead to praise her. But it was obvious from the way she moaned that Anna liked hearing Ruby talk this way to someone else. Obvious from the way that he moved his hips back against her that Dean liked being called names.

"Mmm, so needy," Ruby continued, pushing a third finger inside of him. "Spreading your legs for me, making those pretty noises."

Dean whined and the extra stimulation was just what Anna needed, as she came with a shout. She grinned at Ruby and Ruby grinned back, lathering the strap on with lube and pulling her fingers out of Dean.

She entered him slowly, careful not to hurt him on his first time, but he pressed against her impatiently. She laughed, breathless.

"Eager," she said approvingly as she bottomed out.

She moved against him, pulling out just a little bit before pushing back in, but slowly increasing her movements until she really was fucking him, good and proper. The base of the dildo pressed against her, stimulating her, and the noises Dean made, continuous and loud, only made it sweeter.

Dean reached for his cock and he only managed to stroke it a few times before he was coming with a moan. Ruby stopped fucking him, pulled out while he's relaxed. He collapsed on the bed as soon as she'd pulled all the way out, his legs shaking.

"Fuck, that was hot," Ruby sighed. Anna moaned her agreement into her pillow.

Rubies went to the bathroom to clean the strap-on and by the time she got back, Anna and Dean were already asleep. She slipped between them, playing Anna's little spoon and Dean's big one.

She fell asleep, sated and happy.


	2. Take a Step That Is New

**A/N:** Cas is actually in this part so yay! Still taking my titles from the Three's Company theme 'cause I'm classy like that.

* * *

**Part 2: Take a Step That Is New**

* * *

When Dean woke that morning, it was in an unfamiliar place, aching in unfamiliar ways. It took him a couple of minutes to remember what had taken place the night before - seeing Anna's red head on the pillow next to him helped - and when he did, a sense of accomplishment he'd rarely felt washed over him.

Because seriously, if there was an accomplishment greater than having a threesome with a hot lesbian couple, Dean didn't want to hear about it. He also recalled with no small amount of pride that both women had seemed to enjoy themselves wildly. Anna, as a matter of fact, still had a satisfied little smile on her face, even as she slept. Dean would so be bragging about this later.

The pegging, he could go without mentioning. Or how much he'd liked it.

Which had obviously only happened because he was drunk.

But that had been last night and Dean was no longer drunk, just hung over. The smell of bacon wafting from the kitchen promised to settle his stomach, and Dean figured that he could go and grab a couple of strips before Ruby inevitably kicked him out. She didn't really seem like the morning after type; Dean was honestly a little bit surprised that he hadn't woken up on the curb outside the house.

Dean climbed out of bed, careful so as not to wake Anna, and fished his boxers off of the floor. He could worry about the rest of his clothes once he had filled his stomach. It wasn't like he had anything to be ashamed about.

Dean padded quietly to the kitchen. He came to a short stop by the counter when he realized that the person standing over the pan was not Ruby, or a chick for that matter.

The stranger looked up and blinked, clearly stunned. His eyes dropped down to Dean's bare chest and he reddened. "Who the hell-"

Before he could finish, Ruby walked out of what Dean assumed was the bathroom, drying her hair with a towel. "Morning, Cassie. Dean-o."

Cassie – and Dean didn't believe for one second that that was the guy's real name, so he'd just refer to him by the much less embarrassing 'Cas' – turned his eyes to Ruby and glared. "Did you just cheat on my sister, in her own apartment?" His voice was low and growly and for one second, all Dean could think, absurdly enough, was 'mother, may I?'.

Ruby rolled her eyes, unimpressed. "Chill it, Columbo. Anna was totally in on the fun. In fact, this whole hooking up with a stranger we met at a bar thing was her idea." She smirked. "Don't tell me you didn't hear us. Dean here was very vocal."

Dean flushed because, yeah, he had been. He glanced over to Cas, who looked even redder than Dean felt.

"I thought you were watching a pornographic film," he finally muttered. He couldn't seem to look either Dean or Ruby in the eye, staring instead straight at the sizzling bacon and eggs on the frying pan.

"Yeah, well," Ruby sighed. "I'd say sorry you had to hear that but one, you were supposed to be out and we had no idea you weren't and two..." she smirked, "Two, I'm gonna go out on a limb here and say that you didn't totally hate what you heard."

And great, now Dean couldn't look either of them in the eye either.

"I don't enjoy hearing my sister having sex," Cas protested.

Ruby snorted. "God, I should hope not. I know you guys are close but that would be too close for comfort. I was referring to the pretty noises Dean made. And possibly me." She quirked her head to the side and batted her eyelashes in a super affected way. "Let's face it, I'm pretty irresistible. It's okay to admit that you want me."

"Want you to leave," Cas muttered.

"Oh, fine, I'll leave you two alone." Dean shot Ruby a panicked look. No way was he up to spending any time with this stranger who apparently knew what he sounded like when he got fucked in the ass. This morning after was awkward enough already. Ruby, of course, ignored him. "Don't want Anna to wake up alone anyway, you know how cranky she gets in the morning."

Ruby stood up and stretched. "Better have some bacon ready when we get out of bed. Or just send Dean back in. Either way, I'm craving meat."

Yeah, Dean could never look that Cas guy in the face again. As soon as Ruby slammed the bedroom door shut behind her, an awkward silence descended. What the hell was there to say after a scene like that? Dean kept his eyes on the counter, drumming his finger softly.

Eventually, the silence became too much. "Do you want any help with that?" Dean asked lamely. He cringed at how hoarse his voice sounded; could it be any more obvious what he'd been doing? Not that Cas didn't already know.

"It's fine," Cas said. He clearly didn't want to continue the conversation, so Dean didn't press it.

The minutes stretched on and Dean seriously debated just going back to the bedroom as seeing what Anna and Ruby were up to but somehow that felt like it would be even more painfully awkward than the current situation, so he stayed put.

"I'm sorry," Dean said when he finally couldn't stay quiet anymore. "I had no idea that anyone else was home."

"It's fine," Cas repeated, sounding a little breathy with annoyance. "You had no way of knowing. I should have known better than to come back here when I knew my sister and her girlfriend would be having loud sex. I had intended to stay with my boyfriend but as it turned out, more people were having loud sex than just you three."

Dean's eyebrows flew up. "He was cheating on you."

"Apparently it was never an exclusive relationship," Cas said. "Somehow I failed to understand that." He stabbed at the finished bacon strips and slapped them on a plate with a lot more viciousness than was called for. "I also fail to understand why I am sharing this information with a complete stranger."

"Hey, sometimes it helps to talk." Dean shrugged. "Besides, it's not like we're complete strangers. You know what I sound like during sex, that practically makes us friends."

Dean didn't realize until after he had spoken that his little joke might backfire, that it might make Cas even more annoyed with him than he already was. He was inexplicably relieved when Cas let out a small chuckle.

"You have a strange way of making friends."

Dean smiled. "If you'd seen my o-face, you'd have attained BFF status."

Cas smiled back, a little sheepishly. "I'm sorry, I don't get that reference."

"What, BFF?" Cas nodded. "It means Best Friends Forever, or at least with teenage girls it does."

"I see."

The eggs and the rest of the bacon finished cooking and Cas turned off the stove. Dean helped him set the breakfast table, despite Cas's insistence that as a guest he shouldn't have to. Dean pointed out that he was an unannounced guest in Cas's home, and one that had probably cost him a great deal of a good night's sleep. Cas conceded that, adding that despite Dean being unannounced he certainly wasn't unwelcome, and let Dean help him.

"By the way, my name is Castiel. Not Cassie."

"Yeah, I figured it wasn't." Dean took a sip of orange juice. "Although I thought you'd be a Lucas or a Casper or something. I didn't see 'Castiel' coming."

"If you had, we would be BFF by now."

Dean nearly did a spit-take at that, causing Castiel to look inordinately proud. "Oh my God you asshole, you couldn't have waited until I had swallowed?" Cas raised an eyebrow and Dean started laughing. "Not a word."

Cas's big, blue eyes went even bigger. "I didn't say anything."

* * *

In the end, Ruby and Anna didn't emerge from the bedroom until after Dean had left. Castiel had watched the other man go inside for his clothes (not that Cas could honestly say he minded his state of dress) and come back out fifteen minutes later, fully dressed and looking harried. He gave Castiel a warm smile as he left and Castiel felt a stab of loss at the thought that he might never meet the handsome stranger again. He had a way of talking that left Castiel at a complete ease and that wasn't common. It almost made him forget the fact that he knew what Dean sounded like when he climaxed (almost).

"Cas, I'm so sorry," Anna blurted as soon as she stepped outside the bedroom. "If I'd had any idea you were home-"

"Well, we didn't," Ruby said lazily. "So you've got nothing to be sorry about, Cassie here was the one who promised to stay at his beau's place for the night."

Anna frowned. "Why weren't you at David's place? Did you guys get into a fight?"

Castiel debated not telling her anything, leave it alone for a later time when he was better rested and could actually look his sister in the eye, but ultimately he knew that it wouldn't do any good to put it off. "No," he said truthfully. "But he was sleeping with someone else and we broke up."

"Oh my God," Anna exclaimed. "Are you serious?" Cas nodded. "That asshole is dead!"

"Do you want me to chop his balls off?" Ruby helpfully asked, making a scissoring motion with her fingers. "I can make it look like an accident."

"There's no need to kill David or... chop his balls off." Castiel sighed, circling his cup of coffee with both hands in a nervous gesture.

He hated these kind of talks, he never knew how he was supposed to act. Should he be hurt over David's betrayal? Maybe he was, a little bit, but the two of them hadn't been together for long and they hadn't been in love or anything. Castiel had never pictured them lasting. He was more angry than he was hurt, but he wasn't very angry either. Certainly not as angry as Anna looked to be.

"Our relationship was never exclusive," he continued. "It was just I who assumed it was. We broke it off because we realized we wanted different things."

"The guy's still an asshole," Anna insisted.

"Eh, I always knew he wasn't good enough for you," Ruby said with a shrug. Which was surprisingly sweet of her. Castiel was almost relieved when she completely ruined the sentiment with her next sentence. "I can't believe you're harshing my threesome buzz over this. What you should have done was go out and get laid immediately. No moping around the apartment while you listen to the people in the next room over having amazingly hot sex."

"Ruby," Anna chastised.

Ruby's eyes lit up. "Hey! Speaking of amazingly hot threesome sex!" She stuffed her hand down her shirt and came back up with a small piece of paper. "It's Dean's number. I bullied him into giving it to me before he left." She handed the number to Castiel. "You should call him."

Castiel couldn't even begin to list the ways how terrible an idea that was. Mostly because he was busy thinking about Dean's sweet smile and chiseled upper body. And his eyes, those shining, green eyes, framed by thick eyelashes and how amazing would he look peering up at Castiel through those lashes...

Right. Terrible idea. He held the number out to Ruby. "I can't."

Ruby scoffed, not accepting the small piece of paper back. "Why the hell not?"

"Forgetting the circumstances under which we met," Cas said, "Dean is straight."

"Like hell he is!" Ruby exclaimed. "No straight guy loves taking it up the ass so much."

Anna groaned and hid her reddening face in her hands. Meanwhile, Castiel's brain had short-circuited.

"I... What?"

"Yeah." Ruby nodded. "Dude totally let me peg him. Not just let, he loved every goddamn second of it. Those noises you heard didn't start until I was three fingers in, you know."

Castiel was fairly certain he was about to have a heart attack. "Thank you for the visual. But just because he likes... that, it doesn't have to mean he's anything other than straight."

"Fine." Ruby stood up and went to the couch, where her jacket lay crumbled. She shrugged it on. "Have it your way. Just know that you might be missing out big time if you don't give this dude a call. Come on, Anna. This bacon's cold and I'm craving some donuts."

Anna wordlessly nodded and followed her girlfriend out the front door, too mortified to say goodbye to Castiel.

The door slammed shut and Castiel was left alone in the apartment, Dean's phone number crumbled up in his right hand. Castiel knew he should throw it out. It wasn't like he was ever going to call it, no matter how charming or handsome or easy to talk to he'd found the other man.

It simply wasn't meant to happen.

* * *

Dean was pretty sure that most people did not come out a threesome experiencing a crisis of sexuality. A devil's threeway, maybe, but not the regular kind. It wasn't as if he'd never done anything with another guy; he'd had his fair share of drunken fumbles, enough to know that sometimes, dick was his thing.

But giving someone a handjob or blowing them in a bathroom stall at a bar is one thing. Taking it up the ass is quite another and up until that threesome, Dean had never even considered it. The thought honestly hadn't entered his mind. He'd thought about fucking a guy a few times, but Dean Winchester did not bottom.

Except apparently sometimes he did. And apparently it made for the best sex of his life (well, that and the two hot bi chicks).

There was also Anna's brother, Castiel. Dean was a charming enough guy but he didn't have an easy time making friends. With Cas, though, they'd hit it off right away. Cas was witty in a dry and unconventional way, and he had this unique way of talking that sounded like he'd learnt to talk from books rather than human interaction. Which, okay, maybe wasn't the most flattering description, but Dean couldn't think of anything better. The dude was interesting and Dean liked talking to him. He was also kind of smoking hot.

If they had met under any other circumstance, Dean would have asked for his number. As it were, the circumstances involved Dean having sex with Castiel's sister and her girlfriend, and Castiel knowing what Dean sounded like when he took it up the ass. Not that Cas knew exactly what it was he'd been listening to (thank God), but it took Dean's mind to places. Places that were both terrifying and hot as hell.

This was not something Dean could handle alone. He needed to talk to someone and there was only one someone he knew that he felt comfortable telling everything that happened.

"I love this place," Charlie hummed happily around the coffee stirrer. "The caramel mocha is to die for."

It was a couple of hours before his shift at the Roadhouse and Dean had asked Charlie to meet at a coffee house. He'd made the mistake of letting her pick the place and here they were, in some fruity coffee shop slash bakery that looked like it'd been decorated by either an eight year old girl or an eighty year old woman. Lace and doilies and the color pink everywhere.

But the coffee was good and judging by the smell, the pastries were as well. Dean had ordered himself a slice of apple pie, which was currently in the oven. Charlie had decided to forgo a pastry since her large caramel mocha with whipped cream and chocolate sprinkles was quite enough to give her type two diabetes by itself.

Charlie finally stopped making love to the coffee stirrer and took a sip of her coffee, sighing blissfully. "So what did you wanna talk about?"

"I kind of, uh," Dean said, "I went to the bar last night and had a threesome with a lesbian couple."

Charlie wordlessly held up her hand, which Dean dutifully high fived. "Dude," she said. "I am so jealous I kind of want to drown you in my caramel mocha right now. How did you even manage that?"

"They were looking for someone and I happened to be the lucky one." Dean could totally do humble when need be. Besides, he needed to stay on Charlie's good side right now and bragging was not the right way to go about that. "But it kind of got out of hand."

Charlie raised an eyebrow. "Got out of hand? Dude, you were in a threesome with two, I'm assuming, smoking hot chicks." Dean nodded. "I don't see how anything could possibly go wrong in that scenario. Did they get too involved with each other and forget to get you off?"

"No," Dean said. He glanced around but the tables around them were empty and the nauseating music playing (was that Michael Bublé?) was enough to drown out their quiet voices. "It was going great and then one of them reached into the night stand and pulled out a strap-on."

"And you bolted," Charlie guessed. "Dude, that was like a once in a lifetime opportunity and you ruined it by being all scaredy straight boy..." She trailed off and Dean was suddenly aware of the fact that he was blushing. "No way."

"What?"

Charlie's eyes widened. "No way, you didn't run, did you? You stayed! You stayed and you got fucked up the ass."

And of course at that moment, the waitress arrived with Dean's pie. Worse yet, she looked like someone's grandmother. She put the plate down, gave Charlie a disapproving look and disappeared back into the kitchen.

"Wow, that was painful," Dean said.

"No changing the subject," Charlie chastized. She grinned. "Unless that was right on subject. Is it? I was right, wasn't I?"

Dean rubbed the back of his neck. "Yeah, you were."

"And?"

"And?"

Charlie threw up her hands. "Dude, you're impossible. How was it?"

"I... didn't hate it," Dean admitted. He knew Charlie could read between the lines and tell that 'didn't hate it' meant something else entirely.

"Oh my God," Charlie said.

"Just keep your voice down." Dean took a bite of his pie and almost dropped the fork as he had a spontaneous orgasm on the spot. Well, not really, but it was a near thing. "And for the record, it wasn't painful either."

"Okay, so you got pegged and you're freaking out," Charlie summarized. She took a sip of her coffee. "What am I supposed to say to help you with that? Some people just like taking it up the ass, there's nothing wrong with that."

Dean glared at her, swallowing his mouthful of pie. "So glad I decided to tell you about this. And there's more."

And so he told Charlie about Cas and the painfully awkward morning after, made all the worse by Ruby and her big mouth. Finally, reluctantly, he told her about how after a while, talking with Cas hadn't been awkward at all. It had actually been one of the more interesting conversations Dean had had in a while and now he maybe wished he could meet Cas again.

"I am so telling this story at your wedding," Charlie said when Dean finished speaking.

Dean scowled. "There's not gonna be a wedding, I'm never going to meet him again."

Charlie's eyes widened. "What? After a romantic first meeting like that? Okay, awkward as hell, but the fact that you guys could still talk after all that shows that you had a connection. Why would you let that go?"

"Well, I fucked his sister, for one," Dean said dryly. "A first meeting like that isn't something you just bounce back from. Besides, it's not like I have his number or anything."

"No, but you know where he lives," Charlie pointed out.

"And what am I gonna do with that information, stake out his apartment? I feel skeezy enough already about the whole thing."

Charlie rolled her eyes. "No staking out is required. Just pretend you forgot something at the apartment and drop by to pick it up. And then you ask him out for coffee, you hook up, live happily ever after and I get to make the greatest best man speech ever at your wedding."

"You know if I ever got married, Sam would be my best man," Dean said. He dropped his fork on the now empty plate. "And how could I be sure that he would be home and not, say, his sister?"

"Okay, good point." Charlie scratched her head. "What are you gonna do, then?"

"I already told you, nothing."

"Then why did you tell me all that, if not to get advice on how to proceed?"

That was a good question, one that Dean didn't really know the answer to. His thoughts had been a jumbled mess in his head, still were, and his first priority had been to word them out loud to someone who wouldn't mock him for them. But maybe he'd been hoping for advice, too. What else did he expect to get out of this? All he had right now was a headache.

"I don't know," he finally answered.

Charlie's expression softened. "Okay. It's fine, Dean, you don't have to know right now." She looked at her watch. "We should be heading back to work. But when you do figure out what you want, or at least what kind of help you want from me, I'm always here to talk."

Dean resisted the urge to metaphorically bury his head in the sand at being confronted with all those messy, girly emotions, and simply nodded curtly. "Yeah. Thanks."

"No problem."

* * *

Castiel kept Dean's phone number but he didn't call it. He could practically feel it burning a hole in his wallet (yes, he kept it on him and he was well aware of how pathetic he was being) but the temptation to call never became too great. Certainly, he had enjoyed Dean's company and the other man was attractive enough - flipping gorgeous had been the term that Anna used and Castiel did not necessarily disagree.

But he and Dean had met under very unusual circumstances and while it may be possible for Castiel to look past that, he knew better than to expect that from Dean. After all, how many people would be willing to date someone whom they met through having a one-night-stand with their sister?

Yes, it was tempting to contact Dean but the thought of rejection kept Castiel from reaching into his wallet and dialing that number.

It was three weeks after meeting Dean that Castiel went to a local second-hand bookstore, Singer's Salvage Shop, picking up a birthday gift for Anna. He stopped short as soon as he walked inside because who should be sitting at the counter but Dean.

Of course. It seemed the universe had a sense of humor. It just so happened to be at Castiel's expense.

Castiel closed the door behind him and Dean looked up. Their eyes met from across the store and for a moment, Dean actually looked happy to see him. Then he flushed red and ducked his head, clearly remembering... well, everything from their last encounter.

Briefly, Castiel considered just leaving and coming back later, but Anna's birthday was tomorrow and he wouldn't have the time to pick up her gift then. Besides, who was to say that Dean wouldn't be working here tomorrow, too?

He walked up to the counter. "Hello, Dean."

"Cas," Dean muttered. Then, voice stronger, "Hey. You, uh, you need some help?"

"I'm picking up an order." Castiel was proud of how together he was. Everything about Dean, not just the way they met, seemed designed to leave him flustered. "William Goldberg's The Princess Bride? It should be under Milton."

Dean shot him a small smile (which most empathetically did not send Castiel's heart racing) and reached under the counter. "Yeah, I have it right here. Been in for a while, dude. Did Bobby not tell you when it would be delivered?"

Castiel felt his face heat slightly and hoped he wasn't blushing. "I've been busy."

Dean smirked, demeanor more confident now that Castiel was less so. "I'll bet."

The innuendo didn't make much sense, but the cheeky tone had Castiel even more flustered. He handed Dean his credit card, wanting to finish their transaction before he did or said something monumentally stupid.

But Dean beat him to it. "Do you wanna grab a coffee sometime?"

Okay, so it wasn't monumentally stupid so much as it was wonderful, but Castiel had presence of mind enough to know that had he liked Dean any less, he would have turned him down purely due to circumstance.

Fortunate that he liked Dean as much as he did. "I would like that."

Dean handed him back the credit card. His smirk had softened into a smile. "Yeah?"

"I like you," Castiel said, because he'd never bothered to learn to be anything other than direct. "And unfortunate circumstances aside, I would like to get to know you better."

Dean was silent for a moment. A light flush was making itself apparent on his cheeks. "Should I give you my number?"

"I have it." Castiel only realized afterwards how that might be taken. "Ruby," he added as an explanation.

"Oh." Dean wet his lips. "Right, that makes sense."

Castiel wasn't quite certain how to proceed. "I'll call you?"

Dean nodded. "Awesome."

Castiel took the book into his hand. It had been packed in brown paper and string, and the weight of it in his hand grounded him. He smiled, more confident. Echoed Dean's sentiment, "Awesome."


End file.
